FR2258362A1 - 9-Hydroxy prostaglandins prodn - by reducing 9-oxo cpds with a sodium bis(alkoxy)aluminium dihydride - Google Patents
9-Hydroxy prostaglandins prodn - by reducing 9-oxo cpds with a sodium bis(alkoxy)aluminium dihydrideInfo
- Publication number
- FR2258362A1 FR2258362A1 FR7401942A FR7401942A FR2258362A1 FR 2258362 A1 FR2258362 A1 FR 2258362A1 FR 7401942 A FR7401942 A FR 7401942A FR 7401942 A FR7401942 A FR 7401942A FR 2258362 A1 FR2258362 A1 FR 2258362A1
- Authority
- FR
- France
- Prior art keywords
- reducing
- cpds
- oxo
- alkoxy
- prodn
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 title 1
- 229910052782 aluminium Inorganic materials 0.000 title 1
- 239000004411 aluminium Substances 0.000 title 1
- 229910052708 sodium Inorganic materials 0.000 title 1
- 239000011734 sodium Substances 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Prostaglandins of formula (I) are prepd. by reducing the corresp. 9-oxo cpds. (II) with (R degrees O)2AlNaH2 then hydrolysing; (R = H or lower alkyl; R1 and R2 = H, acetyl or tri(loweralkyl)silyl; Z = single or double bond; R degrees = lower alkyl, tetrahydrofuryl, tetrahydropyranyl or lower alkoxy lower alkyl). These reducing agents are soluble in org. solvents (contrast metal hydrides and borohydrides) so give more complete redn. of (II). Reaction is generally at room temp. in a solvent such as hydrocarbons, alcohols, ethers or O-contg. heterocycles. The Al-contg. intermediate is pref. hydrolysed with acid, esp. a stoichiometric amt. of HCl, HBr, H2SO4, H3PO4 or acetic acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7401942A FR2258362A1 (en) | 1974-01-21 | 1974-01-21 | 9-Hydroxy prostaglandins prodn - by reducing 9-oxo cpds with a sodium bis(alkoxy)aluminium dihydride |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7401942A FR2258362A1 (en) | 1974-01-21 | 1974-01-21 | 9-Hydroxy prostaglandins prodn - by reducing 9-oxo cpds with a sodium bis(alkoxy)aluminium dihydride |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2258362A1 true FR2258362A1 (en) | 1975-08-18 |
FR2258362B3 FR2258362B3 (en) | 1976-11-05 |
Family
ID=9133740
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7401942A Granted FR2258362A1 (en) | 1974-01-21 | 1974-01-21 | 9-Hydroxy prostaglandins prodn - by reducing 9-oxo cpds with a sodium bis(alkoxy)aluminium dihydride |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2258362A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0410786A1 (en) * | 1989-07-27 | 1991-01-30 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins |
-
1974
- 1974-01-21 FR FR7401942A patent/FR2258362A1/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0410786A1 (en) * | 1989-07-27 | 1991-01-30 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins |
Also Published As
Publication number | Publication date |
---|---|
FR2258362B3 (en) | 1976-11-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |